92+ Hotel & Resort Deals in Southwest Side |
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Southwest Side Hotels, Resorts, and Rentals

About Southwest Side Vacation Rentals

There are more than 92 places to stay in Southwest Side that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Southwest Side.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Southwest Side, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Southwest Side. Places to stay near Southwest Side are 382.72 ft² on average, with prices averaging US $208 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Southwest Side with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Southwest Side

Type Count
Holiday Apartments 48
Vacation Homes 33

Use these Quick Filters to Find a Vacation Rental in Southwest Side

★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Southwest Side.

Weather in Southwest Side, IL

View the weather forecast for Southwest Side before booking your Southwest Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Southwest Side's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Southwest Side's top attractions, neighborhoods, and points of interest.


Marquette Park
S.S. Peter and Paul Church
Churches of Ukrainian Village
Balzekas Museum of Lithuanian Culture
Crawford Medical Arts
Holy Cross Hospital
University of Illinois Mile Square Health Center
St. Bernard Hospital
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
United Center
Grant Park
John G. Shedd Aquarium

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Canaryville 888 Properties
McKinley Park 739 Properties
Ducktown 686 Properties
Englewood 335 Properties
New City 295 Properties
Back of the Yards 277 Properties
Brighton Park 123 Properties
Garfield Ridge 123 Properties
Archer Heights 109 Properties
West Lawn 103 Properties
Chicago Lawn 95 Properties
Gage Park 88 Properties

Frequently Asked Questions About Southwest Side?

What are the top hotels or resorts in Southwest Side?

You have a lot of choices in or near Southwest Side. If you need a hotel in the Southwest Side area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Southwest Side:

How many vacation rentals have private pools in Southwest Side?

There are 1 accommodation options with private pools in or near Southwest Side. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

How many hotels, resorts, or rentals are available in Southwest Side?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 92 in the Southwest Side area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Southwest Side.

Nearby Neighborhood (16) 
Neighborhood Property Count
Heart of Chicago Hotel & Resort Deals in Chicago, Illinois 27
Greater Grand Crossing Hotel & Resort Deals in Chicago, Illinois 471
Bridgeport Hotel & Resort Deals in Chicago, Illinois 1353
New City Hotel & Resort Deals in Chicago, Illinois 295
Back of the Yards Hotel & Resort Deals in Chicago, Illinois 277
Brighton Park Hotel & Resort Deals in Chicago, Illinois 123
Canaryville Hotel & Resort Deals in Chicago, Illinois 888
Ashburn Hotel & Resort Deals in Chicago, Illinois 109
West Lawn Hotel & Resort Deals in Chicago, Illinois 103
Chicago Lawn Hotel & Resort Deals in Chicago, Illinois 95
McKinley Park Hotel & Resort Deals in Chicago, Illinois 739
Ducktown Hotel & Resort Deals in Chicago, Illinois 686
Englewood Hotel & Resort Deals in Chicago, Illinois 335
Archer Heights Hotel & Resort Deals in Chicago, Illinois 109
Gage Park Hotel & Resort Deals in Chicago, Illinois 88
Clearing Hotel & Resort Deals in Chicago, Illinois 126

People Also Ask

There are 6 hotels in Southwest Side and 81 rentals

Recently Booked Hotels, Resorts, or Rentals in Southwest Side